Halogenated phenols for diagnostics, antioxidant protection and drug delivery

Abstract

The present invention provides compositions and methods for the targeted delivery, release and/or formation of a drug compound at a target site(s) within the body of an individual, such as a diseased and/or inflamed tissue in the body of the individual. These compositions may comprise a halogenated phenol ring cleavably linked to a core structure of a drug compound. Due to the variety of substituents that may be utilized in forming the different types of linkages, numerous examples of drug compounds linked to a halogenated phenol ring are proposed. The present invention further provides compositions comprising halogenated phenol starting compounds that do not undergo cleavage during a dehalogenation reaction to form a drug compound in a targeted tissue when administered to an individual. Methods of administering these non-cleaving compounds are further provided.

What is claimed is: 
     
       1. A compound having the following chemical structure: 
       
         
           
           
               
               
           
         
         wherein R 2  is one of hydrogen, bromine, or iodine, R 3  and R 4  are each a respective hydrogen, wherein X is a halogen, wherein Y is an ether oxygen, wherein R 1  is a core structure of a drug compound, wherein the drug compound is L-DOPA, wherein the halogen is bromine or iodine, and wherein Y is bonded to a phenol ring of the core structure of the drug compound. 
       
     
     
       2. The compound of  claim 1 , wherein the ether linkage (—Y—) between the halogenated phenol ring and the core structure of the drug compound is in the ortho-position relative to the hydroxyl group of the halogenated phenol ring adjacent to the halogen (X), and wherein the compound has the following chemical structure: 
       
         
           
           
               
               
           
         
       
     
     
       3. The compound of  claim 1 , wherein the ether linkage (—Y—) between the halogenated phenol ring and the core structure of the drug compound is in the meta-position relative to the hydroxyl group of the halogenated phenol ring adjacent to the halogen (X), and wherein the compound has the following chemical structure: 
       
         
           
           
               
               
           
         
       
     
     
       4. The compound of  claim 1 , wherein the ether linkage (—Y—) between the halogenated phenol ring and the core structure of the drug compound is in the para-position relative to the hydroxyl group of the halogenated phenol ring adjacent to the halogen (X), and wherein the compound has the following chemical structure: 
       
         
           
           
               
               
           
         
       
     
     
       5. The compound of  claim 4 , wherein R 2  is either iodine or bromine. 
     
     
       6. The compound of  claim 4 , wherein R 2 , R 3  and R 4  are each a hydrogen. 
     
     
       7. The compound of  claim 1 , wherein the ether linkage (—Y—) between the halogenated phenol ring and the core structure of the drug compound is in the meta-position relative to the hydroxyl group of the halogenated phenol ring adjacent to the halogen (X), and wherein the compound has the following chemical structure: 
       
         
           
           
               
               
           
         
       
     
     
       8. The compound of  claim 1 , further comprising a pharmaceutically acceptable carrier. 
     
     
       9. A compound having the following chemical structure: 
       
         
           
           
               
               
           
         
         wherein R 2  is one of hydrogen, bromine, or iodine, R 3  and R 4  are each a respective hydrogen, and wherein X is a halogen, wherein the halogen is either bromine or iodine. 
       
     
     
       10. The compound of  claim 9 , wherein R 2 , R 3  and R 4  are each a hydrogen. 
     
     
       11. The compound of  claim 9 , wherein the ether linkage between the halogenated phenol ring and the core structure of the drug compound is in the para-position relative to the hydroxyl group of the halogenated phenol ring adjacent to the halogen (X). 
     
     
       12. The compound of  claim 9 , having the following chemical structure: 
       
         
           
           
               
               
           
         
       
     
     
       13. The compound of  claim 9 , having the following chemical structure: